


Drabble #16 - Dean "totally straight" Winchester

by arinwrites



Series: Destiel Drabbles [16]
Category: Supernatural
Genre: Alternate Universe - High School, Bottom Dean, Jock Dean Winchester, M/M, Punk Castiel, Smut, Top Castiel
Language: English
Status: Completed
Published: 2016-02-20
Updated: 2016-03-08
Packaged: 2018-05-22 02:04:29
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,664
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6066529
Author URL: https://archiveofourown.org/users/arinwrites/pseuds/arinwrites
Summary: <blockquote class="userstuff">
      <p>Breaking top!dean stereotypes since 2014.</p>
    </blockquote>





	1. Chapter 1

**Author's Note:**

> Breaking top!dean stereotypes since 2014.

Cas stood by his locker, feeling almost  annoyed. He quickly pulled on his jacket and slipped a lighter in next to the pack of cigarettes in his pocket. It was almost the end of lunch but there was no way that he was sitting through math class after that shitty first half of the day. He thought that he was all clear to get out of the shithole when he saw none other than Dean Winchester walking towards him, which considering the mood he was in, would most likely be a bad thing.

Dean walked up to the guy with a smirk on his face, ready to keep his asshole jock title. "Where do you think you're going, Novak?" He didn't necessarily like doing it, but highschool was all about status; the popularity hierarchy. Even if this Castiel Novak guy was hot, he couldn't be caught dead with another guy, which is how he developed the cocky attitude and the heteronormativity that had built a wall in front of the bisexual tendencies in his brain. Well uh...mostly. He had his guilty pleasures.

Cas rolled his eyes, stepping closer to Dean without a fear. Normally he would just scoff and walk away, but today? He'd dealt with enough shit. He didn't need any of this bullcrap fake attitude from none other than Dean Winchester. He said fake because he knew that Dean wasn't straight and he knew that he didn't hate Cas. In fact, he knew that Dean liked him. It was all in the body language, the way that he looked at Cas when he thought no one saw him. To anyone else it was rivalry, but Cas saw right through the act. "You know what, Winchester? You can drop the charade, buddy." Cas scowled, moving closer with determination.

Dean's hands raised in front of his chest in defense, a look of false confusion plastered on his face. God, Cas just wanted to punch it right off. "Charade? We both know that I hate your guts, Novak. Why would that ever change?" Dean chuckled softly, the tone bordering on evil.  It killed him a little inside to talk to the guy he'd had a crush on for years like this, but damn he was selfish and he wasn't throwing away his reputation.

Cas face shifted to a fake sympathetic frown, walking even closer to Dean as he abandoned all sense of personal space. Well if he had to bring out the gay in Dean Winchester than so be it. There was no turning back now. "Oh, but we both know that's not quite true, don't we?" Dean pretended to be discusted by what Cas hinted at with those words, pretended to be the bigoted homophobe that he was supposed to be as he scrunched up his nose. "I don't know what you're talking about, man." Dean's voice had flatlined, each monotone word spoken with less meaning than the next.

Cas rolled his eyes and licked his lips, giving Dean a good look at the tongue piercing in his mouth as he got ready to bring in the big guns. His right hand reached out to to rest on Dean's shoulder as he watched the other boy try to replace his real reaction with an unpleasant one. "Listen, if you want to step around it. If you want to pretend that you hate me be my guest, but I know your secret." His hand slowly traveled down, a featherlight touch along Dean's left side. Dean struggled to keep a straight face, the wall of sexual repression in his head breaking down. "You can pretend that you aren't thinking about my tongue piercing sliding along your cock, but the truth is..-" Cas' hand slid down to grab Dean's ass as he leant forward to whisper in his ear. "I know how much you want me."

Dean couldn't help but let out a small pathetic whimper at the different sensations running through his body as a clear erection started showing up in his jeans, but he still made one valiant effort to retain a small sliver of masculinity. "And what makes you think I'd be the bottom in that relationship, huh?" Dean internally cringed at his own words, knowing that he would regret tham soon enough as Cas chuckled softly, moving closer if that were even possible. "Think, baby girl? I know." Cas was effectively feeling Dean up in the hallway now, his left hand joining the party.

Dean was nearly gone at that point and completely ready to let Cas have his way, but there was still a slight worry in his mind. Now was the worst time. He had to- it was- he really shouldnt have...damn why did this have to happen today. This day out of all days, the one day that he decided to- his thoughts were rudely interrupted by Cas' words, begging him to surrender to his desires. "C’mon baby, I know where we can go." He smirked, pressing the palm of his hand to the bulge in Dean's jeans, watching him struggle to hold back a moan. "I've gotta take care of this for you."  
. . . . .

Cas pushed Dean into the backseat of his car gently, slamming the door behind himself and immediately going to unbutton Dean's pants. He knew that he was supposed to be the one teasing Dean, but Cas was just as eager. He also didn't know the next time that he would have Dean Winchester laying in front of him and practically begging to be fucked. The gravity of the situation really set it when Cas pulled Dean's jeans down around his ankles, mouthing lightly at the outline of Dean's cock through his boxers.

Cas must have won the lottery because Dean was a very sensitive guy, little moans and gasps and whimpers filled the air at the smallest touches, and he hadn't even gotten to the actual thing yet. Cas tortourously slowly started to tug down Dean's boxers inch by inch, looking up to gauge his reaction. Dean was loving it of course, but his expression also gave off another message, one of extreme embarrassment even though there wasn't enough blood in his body to make his face flush red. "What's wrong, Winchester? Got something to hide?" Cas smirked, pressing some kisses down Dean's stomach and towards where he wanted them the most.

Dean bit his lip, his back arching slightly so that he could press against Cas' mouth. With how good this felt he was wondering why he'd ever let those assholes stop him from being with guys, he forgot how fucking amazing it was. When his boxers were pulled completely down he drew in a sharp breath, one of fear and anticipation, his eyes averting Cas' briefly as he bit his tongue.

Cas was equally confused and excited to find out what the hell Dean was so nervous about that could be under those boxers. He had never seen Dean so flustered and shameful in his life. It was when he finally pulled those boxers down that he could help but chuckle, seeing exactly what Dean was so embarrassed about. "So this is what you're hiding, huh?" Cas' finger tapped twice against the base of a fairly sized silicon plug lodged inside of Dean, watching him squirm as it brushed against his prostate. "I- it's not.." Dean struggled to formulate a legitimate reply, only stutters and pieces of sentences coming out.

"Oh, no I get it." Cas smirked, twisting the plug teasingly. "You're definately not a bottom, Winchester." With that Cas went to work, dragging his tongue piercing across the head of Dean's cock just like he had promised as he pushed the plug in and out slowly just to drive Dean crazy. After about ten seconds Dean already looked like he was ready to come down Cas' throat, which as great as it sounded, Cas was not going to let that happen. Not until he replaced that plug with the real thing, which was the only thing on his mind as pulled away to unbuttoned his own jeans and free his erection quickly.

The sight of Cas' cock had Dean more than ready to erase years of forced heterosexuality as he reached down to the plug still firmly pressed into him, planning to pull it out but being interrupted half way by Cas' hand swatting his away. "I'll get it. I don't need any funny buisness from you, pretty boy." Cas slowly began pulling it out, watching the way that Dean's rim stretched around it just a little too closely and listening to Dean whimper for something in it's place immediately after it was gone.

Of course, he wasn't going to give Dean exactly what he wanted right away. That would be too easy, but Dean was definately not complaining when a curious finger pressed into him, searching for and almost immediatley finding his prostate as Dean held onto the seat under him for dear life. He also wasn't complaining about how un-lawfully amazing that metal ball on Cas' tongue felt as it circled around his rim, making him moan for more until Cas stopped.

"You really do want me, huh?" Cas teased the tip of his cock against Dean's entrance, chuckling as Dean tried desperately to push back onto it. "So eager, aren't you?" In seconds a devilish idea popped into Cas' head, his hands moving to hold Dean's hips still. "If you're so eager, why don't you _beg for me._ "


	2. Chapter 2

**Notes for the Chapter:**

> Well this is about 1,000 word longer than usual so enjoy that. Maybe it's a late fee on my part. I meant to finish this last week but I came down with a stomach bug and lived off club crackers and 7up for three days. So anyway, I'm better now and I hope the people who were waiting for this enjoy.

Dean looked at Cas with desperation in his eyes, a kind of needy and terrified expression on his face. "Cas, I can't-" A switch flipped in Cas' mind, something of dominance and control as he landed a harsh spank on Dean's ass, a red imprint of where his hand had been resting there and slowly fading away. "I know you can- unless you don't want my cock inside of you anymore...what a shame that would be after waiting this long." Cas' dick brushed up against Dean's hole again, making a breathy moan escape both of their lips. 

Dean had no chance of getting what he wanted, Cas' hands holding onto Dean's hips with more pressure than he had originally expected. How close Cas was to being inside of him was borderline torturous, finally breaking him and making him beg for more. "Cas, please- more. I need your cock inside of me." One of Dean's hands travelled down to his own ass without permission, helping to spread his cheeks apart in hopes that Cas would take the invitation. 

Cas of course, did not, although it was tempting when he saw how open and ready Dean was for him, spreading his legs even wider for Cas to admire. At that point Cas decided that he wanted Dean's ass on display even more, and Dean certainly wouldn't say no to that. "On your knees, pretty boy. I wanna see that amazing ass of yours." Cas smirked as Dean scampered to turn around, sticking his ass into the air without being asked like the submissive bottom he really was. 

There was no warning of any sort before Cas' hands spread Dean's cheeks apart, his tongue going back to work just as it had earlier, teasing around Dean's rim and occasionally pressing into his hole slightly. Dean's mouth hung open in nearly noiseless pleasure, nothing but a few needy whimpers and broken sentences to break the silence. "Y-yes, Cas. Don't stop- so good." Dean pushed back onto Cas' tongue like it was his main life source, moaning just a little too loudly when one of Cas' fingers pushed in next to it and brushed against his prostate slightly. 

If Cas was being generous he would have stopped right there, but this was Dean Winchester who had proven himself to be a needy and eager individual, so any thought of letting him off the hook easy had disappeared. A second finger slipped in easily because of how stretched Dean had already been prior to its entrance, the agonizing wait for something more making Dean whimper pathetically. Cas just couldn't help himelf, removing his fingers so that he could spank Dean's ass again before giving it a gentle squeeze with both of his hands and pulling away completely. "Are you ready now, Winchester?" Cas' voice was gravely and little more intimidating when it was deepened with lust, Dean's breath hitching slightly as a hand swatted his ass for the third time. 

He was more than ready for what Cas had to offer, desperate for anything that was more than a few fingers so that he could finally get some relief. “Yes, Cas. Please- I need something.” Dean arched his back, sticking his ass into the air even farther for Cas to admire. Cas wanted to, he really wanted to, but teasing Dean was just so fun. “Are you sure that you want it? Are you sure that you deserve it?” He positioned himself to push inside of Dean, but he didn’t apply enough force to do so, instead teasing around the rim like before and leaning forward to whisper in Dean’s ear. “I wouldn’t want to ruin your reputation, Winchester.” The noise of one final hard smack on Dean’s ass rang through the car.

Dean whimpered pathetically, grinding his ass back against Cas’ cock and moaning as precome dripped from his own and onto the car seat below him. He had a feeling that he’d be paying for that later. He also had a feeling that he wasn’t going to last too long when Cas finally was inside of him, especially with the unhealthy amount of pleasure he was getting from the exceptionally rough treatment he was receiving. “Yes, yes, I’m sure.” He sounded almost frantic, like he might just die if Cas decided not to fuck him.

Cas contemplated his options for a moment before deciding on what he wanted, or more accurately what he wanted Dean to do. Nothing was ever fun if it was too easy. “Well, if you want it then you have to work for it. Why don’t you ride my cock and show me what you’ve got, baby?” Dean’s eyes widened when it was suggested, practically salivating at the thought. Getting fucked by Castiel Novak, that was one thing, but riding his cock was a fucking wet dream times one thousand that had Dean turning around at the speed of light to lock his lips with Cas’ immediately. 

Cas was caught slightly off guard by the sudden change of pace, but he wasn’t going to complain about a mouthful of Dean Winchester’s tongue along with an overly enthusiastic attitude towards having a dick in his ass. He quickly pulled the other boy into his lap, looking up at him once they had finally broken the kiss, his hands resting firmly on that beautiful ass of his. “You’re perfect, Winchester. So eager.” Cas pressed a few kisses to Dean’s neck, adding a playful bite just for good measure.

Dean looked back at Cas once he had finished with puppy dog eyes and strong-willed determination to finally feel full and sated. “Can I?” He cautiously reached for Cas’ cock, lining it up with his entrance impatiently. Cas normally wouldn’t have stood for that kind of behavior but for once he let it slide, nodding for Dean to continue and groaning with a smile on his face as he sunk onto his length slowly. Dean on the other hand stayed fairly quiet besides a sharp intake of breath and a few tiny whimpers as he adjusted to the feeling. It was more satisfying than anything considering how long he had waited, but Cas was quite…sizeable and it took a second to get used to that.

Once Dean had managed all of Cas’ length he was in heaven, his eyes closed and a pleasantly satisfied expression crossing his face as he hummed contently. The feeling was definitely mutual, though Cas was resisting the urge to start moving; however, his hands did move to Dean’s in preparation to get things going. He did have to admit that Dean’s blissed out expression of pleasure and contentment was a beautiful sight, even if he was getting slightly impatient. His patience though, was no longer a problem when Dean started to roll his hips gently with a soft moan, lifting himself up and down slowly in an attempt to get a rhythm going. 

Cas eagerly complied, thrusting up into Dean and putting his hands that rested on Dean’s hips to good use as they helped the upward and downward motion. Dean was doing most of the work, his pace speeding up just slightly in an effort to escalate the pleasure as he pulled Cas’ lips onto his own again. Their kisses were significantly sloppier than before, most likely because of the current situation, but neither of them really cared as Dean slammed himself down onto Cas’ cock with much more force than before, catching himself off guard in the process with a louder than usual moan as he inadvertently caused Cas to nail his prostate. 

They only broke the kiss to exchange a few words, Cas in particular. Dean let out another moan of pleasure as Cas hit the spot again. “Do you think you can come just like this?” Cas kissed him again, seemingly just for emphasis as he attempted to hit that special place inside of Dean repeatedly. “I want you come from nothing but my cock, just me fucking you senseless.” Dean held back a whimper as waves of pleasure wracked his body, more than certain that he could come from this alone. “Can you do that for me, baby? Come on my cock?” Dean couldn’t suppress a moan that time, bouncing up and down on Cas’ length with much more enthusiasm than before as he got closer to the edge.

“Fuck yes, I could ride you all day, Novak.” Dean’s eyes had long since screwed shut in pleasure, now effectively helping to make Cas hit his prostate on every downward shift and upward thrust. It really wouldn’t be long before Dean was making a mess of himself at this rate, broken moans leaving his mouth periodically. “I’m close, Cas. Gonna come soon.”

Cas was more than ready for Dean to come, eager to feel the way his ass tightened and pulsated around his cock when he finally did fall over the edge. Regardless of Cas’ readiness, Dean did try to hold onto some self-control for as long as physically possible, but it wasn’t long before he was slamming himself down onto Cas and begging for more. Cas definitely gave him what he wanted, his grip on the other boy’s hips tightening as he pulled him down harder and watched him fall apart slowly. “Come on baby, let go. I’m ready for you.”

That was all Cas had to say and Dean was gone, coming onto himself and Cas while trying to be respectful and not make a mess, which proved to be slightly difficult. It wasn’t a big deal however, and Cas ended up pulling a spare t-shirt from somewhere to clean up anything left over. It was then that Dean realized that Cas hadn’t come yet, wondering why he hadn’t said anything. Dean was more than eager to help him out, even if he was out of breath and had already came, he was still eager as hell and he definitely had a plan. “Cas, fuck me.” 

Cas looked slightly surprised at the seemingly needy and still eager demand, but he was more than prepared to deliver. “Are you sure? You already-“ Cas was rudely interrupted by Dean moving off of his lap and back to his original position, his ass straight up into the air for Cas’ viewing pleasure. Dean was fully aware that he wasn’t coming again, but he definitely wanted Cas to. He also wouldn’t mind getting screwed for just a few more minutes just because it felt damn good, especially after coming because he was oversensitive and ready to go. “Yes. Please, fuck me. I need you to come inside of me.” Dean wiggled his butt just a little to tease, grinning to himself when Cas almost immediately repositioned himself and thrust inside. 

Fuck. It was even better than before. Every sensation was borderline painful because of the amount of pleasure it caused, and Dean couldn’t get enough. Dean moaned and begged for more, even though he wasn’t chasing his high anymore. Cas thought that he must have been dreaming because this was the best thing ever. He was getting off on Dean’s moans and noises of pleasure, the other boy’s willingness and submissive nature turning him on even more than he had been before. As Dean pushed back onto Cas and begged for more, Cas could feel himself getting closer and closer by the second, that feeling in his gut really kicking in and before he knew it he was falling over the edge. “Shit- Dean, I’m coming- fuck, I’m coming.”

Dean just went along for the ride, encouraging Cas and moaning as he felt Cas’ release fill him up. “God yes, Cas.” He couldn’t help the unwelcome words from slipping out, something forcing them out of his mouth. He could have honestly said that that was the best sex that he had ever had.

When Cas pulled out Dean let out a shaky breath, nearly falling limp onto the seat below him before he felt something push back in, the familiar feeling of the plug from earlier sliding in to fill the space. Cas leaned over to whisper into Dean’s ear, giving the plug one final push. “You save that in there and I’ll give you more later.” Cas let hit breath hit Dean’s neck, making him shiver slightly. “For now I’m driving you back to my place, you’ll need some rest for next time.” Dean grinned, more than curious about what next time would entail.

**Notes for the Chapter:**

> I hope Cas has tinted windows in that car of his.

**Author's Note:**

> Alternatively titled "Surprise Buttplug"


End file.
